data_2202616
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1509
_journal_page_last  o1511
_publ_section_title
;
3-Isopropylamino-7-nitro-1,4,2-benzothiadiazine 1,1-dioxide
;
loop_
_publ_author_name
  "Dupont, L\'eon"
  'Somers, Fabian'
  'De Tullio, Pascal'
  'Pirotte, Bernard'
_chemical_formula_moiety  'C10 H11 N3 O4 S2'
_chemical_formula_sum  'C10 H11 N3 O4 S2'
_chemical_formula_iupac  'C10 H11 N3 O4 S2'
_chemical_formula_weight  301.34
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  7.4143(7)
_cell_length_b  21.461(4)
_cell_length_c  8.3958(11)
_cell_angle_alpha  90.00
_cell_angle_beta  101.840(12)
_cell_angle_gamma  90.00
_cell_volume  1307.5(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.531
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  S1 0.22976(9) 0.09769(3) 0.11063(8) 0.0417(3) Uani d . 1 . . S
  N2 0.3981(3) 0.14534(10) 0.1511(3) 0.0459(6) Uani d . 1 . . N
  C3 0.5667(4) 0.12775(13) 0.1460(3) 0.0430(6) Uani d . 1 . . C
  S4 0.65181(9) 0.05028(3) 0.15770(9) 0.0479(3) Uani d . 1 . . S
  C5 0.4841(4) 0.00923(13) 0.2358(3) 0.0425(6) Uani d . 1 . . C
  C6 0.5389(4) -0.04736(14) 0.3117(4) 0.0505(7) Uani d . 1 . . C
  H6 0.6600 -0.0607 0.3214 0.061 Uiso calc R 1 . . H
  C7 0.4167(4) -0.08335(15) 0.3718(4) 0.0537(7) Uani d . 1 . . C
  H7 0.4523 -0.1217 0.4194 0.064 Uiso calc R 1 . . H
  C8 0.2376(4) -0.06151(14) 0.3606(3) 0.0452(6) Uani d . 1 . . C
  C9 0.1786(4) -0.00546(13) 0.2874(3) 0.0437(6) Uani d . 1 . . C
  H9 0.0589 0.0086 0.2823 0.052 Uiso calc R 1 . . H
  C10 0.3026(3) 0.02921(12) 0.2217(3) 0.0406(6) Uani d . 1 . . C
  N11 0.6957(3) 0.16836(11) 0.1314(3) 0.0486(6) Uani d . 1 . . N
  H11 0.798(5) 0.1592(19) 0.143(4) 0.058 Uiso d . 1 . . H
  C12 0.6659(4) 0.23559(13) 0.1002(4) 0.0508(7) Uani d . 1 . . C
  H12 0.5338 0.2427 0.0601 0.061 Uiso calc R 1 . . H
  C13 0.7255(8) 0.27127(18) 0.2564(6) 0.0918(15) Uani d . 1 . . C
  H13A 0.6584 0.2566 0.3354 0.138 Uiso calc R 1 . . H
  H13B 0.7012 0.3148 0.2366 0.138 Uiso calc R 1 . . H
  H13C 0.8551 0.2652 0.2970 0.138 Uiso calc R 1 . . H
  C14 0.7657(7) 0.2553(2) -0.0292(6) 0.0967(15) Uani d . 1 . . C
  H14A 0.8961 0.2515 0.0110 0.145 Uiso calc R 1 . . H
  H14B 0.7358 0.2978 -0.0586 0.145 Uiso calc R 1 . . H
  H14C 0.7291 0.2291 -0.1231 0.145 Uiso calc R 1 . . H
  N3 0.1082(4) -0.09914(13) 0.4297(3) 0.0554(7) Uani d . 1 . . N
  O1 0.1917(3) 0.08075(10) -0.0577(2) 0.0548(5) Uani d . 1 . . O
  O2 0.0799(3) 0.12379(10) 0.1739(3) 0.0563(6) Uani d . 1 . . O
  O3 -0.0370(3) -0.07592(12) 0.4450(3) 0.0640(6) Uani d . 1 . . O
  O4 0.1545(4) -0.15259(13) 0.4707(4) 0.0868(9) Uani d . 1 . . O
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  S1 0.0373(4) 0.0340(4) 0.0531(4) 0.0036(2) 0.0077(3) 0.0022(3)
  N2 0.0402(12) 0.0332(11) 0.0647(14) 0.0035(9) 0.0115(10) -0.0021(10)
  C3 0.0454(15) 0.0340(13) 0.0485(13) -0.0013(11) 0.0068(11) -0.0049(11)
  S4 0.0415(4) 0.0346(4) 0.0701(5) 0.0036(3) 0.0174(3) -0.0013(3)
  C5 0.0397(13) 0.0374(14) 0.0505(14) 0.0030(11) 0.0094(11) -0.0033(11)
  C6 0.0436(15) 0.0404(15) 0.0666(17) 0.0079(12) 0.0093(13) 0.0042(13)
  C7 0.0522(17) 0.0412(14) 0.0653(18) 0.0041(13) 0.0064(14) 0.0058(13)
  C8 0.0445(14) 0.0420(14) 0.0486(14) -0.0026(12) 0.0084(11) 0.0026(12)
  C9 0.0413(14) 0.0382(14) 0.0508(14) 0.0000(11) 0.0078(11) -0.0019(11)
  C10 0.0409(13) 0.0334(13) 0.0464(13) 0.0035(11) 0.0066(10) -0.0011(10)
  N11 0.0398(12) 0.0347(12) 0.0714(15) -0.0005(10) 0.0115(11) 0.0021(11)
  C12 0.0454(15) 0.0351(14) 0.0688(18) -0.0012(12) 0.0044(13) 0.0076(13)
  C13 0.123(4) 0.046(2) 0.092(3) 0.001(2) -0.012(3) -0.0123(19)
  C14 0.104(3) 0.078(3) 0.116(4) 0.010(3) 0.042(3) 0.040(3)
  N3 0.0539(15) 0.0526(15) 0.0577(14) -0.0073(12) 0.0066(11) 0.0100(11)
  O1 0.0609(13) 0.0482(12) 0.0518(11) 0.0017(10) 0.0034(9) 0.0029(9)
  O2 0.0415(11) 0.0459(12) 0.0845(14) 0.0101(9) 0.0199(10) 0.0066(11)
  O3 0.0532(13) 0.0689(16) 0.0716(14) -0.0041(11) 0.0166(11) 0.0075(12)
  O4 0.0747(17) 0.0568(15) 0.131(2) 0.0000(13) 0.0253(16) 0.0353(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1 O1 . 1.430(2) no
  S1 O2 . 1.440(2) no
  S1 N2 . 1.595(2) yes
  S1 C10 . 1.765(3) yes
  N2 C3 . 1.315(3) yes
  C3 N11 . 1.318(4) yes
  C3 S4 . 1.774(3) yes
  S4 C5 . 1.757(3) yes
  C5 C6 . 1.393(4) no
  C5 C10 . 1.394(3) no
  C6 C7 . 1.364(4) no
  C6 H6 . 0.9300 no
  C7 C8 . 1.393(4) no
  C7 H7 . 0.9300 no
  C8 C9 . 1.381(4) no
  C8 N3 . 1.462(4) yes
  C9 C10 . 1.382(4) no
  C9 H9 . 0.9300 no
  N11 C12 . 1.475(4) yes
  N11 H11 . 0.77(4) yes
  C12 C14 . 1.496(5) no
  C12 C13 . 1.505(5) no
  C12 H12 . 0.9800 no
  C13 H13A . 0.9600 no
  C13 H13B . 0.9600 no
  C13 H13C . 0.9600 no
  C14 H14A . 0.9600 no
  C14 H14B . 0.9600 no
  C14 H14C . 0.9600 no
  N3 O3 . 1.217(4) yes
  N3 O4 . 1.226(4) yes